Cesium carbonate → N-[4-Methyl-5-(5-phenylsulfonylpyridin-3-yl)-1,3-thiazol-2-yl]acetamide

Participants

Reaction Conditions

Reaction Steps

A mixture of N-[5-(5-bromopyridin-3-yl)-4-methyl-1,3-thiazol-2-yl]acetamide (26 mg), sodium benzenesulfinate (17 mg), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (2.9 mg), caesium carbonate (41 mg) and toluene (3 mL) was purged with nitrogen. Tris(dibenzylideneacetone)dipalladium(0) (1.9 mg) was added and the reaction mixture was heated to 110° C. for 16 hours under a nitrogen atmosphere. A further portion of sodium benzenesulfinate (14 mg) and DMF (1 mL) were added and the reaction mixture was transferred to a microwave vial and heated in a microwave apparatus to 145° C. for 4 hours. The resultant mixture was evaporated and the residue was partitioned between dichloromethane and water. The organic phase was washed with brine, dried over magnesium sulfate and evaporated. The residue was purified by ‘basic reversed-phase chromatography’ as described hereinbefore. There was thus obtained the title compound as a solid (7 mg); 1H NMR Spectrum: (DMSOd6) 2.24 (s, 3H), 2.42 (s, 3H), 7.72 (m, 2H), 7.81 (m, 1H), 8.17 (m, 2H), 8.37 (m, 1H), 9.01 (m, 1H), 9.12 (m, 1H), 12.32 (s, 1H); Mass Spectrum: M+H+ 374.

Provenance & Evidence